Acetic Acid → 2-(3,5-Dimethylphenyl)-1H-indol-5-amine

HRID 1531549Notes

Reaction equation

HRID 1531549 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([N+:18]([O-])=O)=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(O)(=O)C.[H][H]>O1CCCC1.CO.[OH-].[OH-].[Pd+2].O>[CH3:8][C:6]1[CH:5]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([NH2:18])=[CH:13][CH:12]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 21254069HCID 21254069, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 212541012-(3,5-Dimethylphenyl)-1H-indol-5-amine

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(3,5-dimethylphenyl)-5-nitro-1H-indole (2 g in a mixture of 55 mL tetrahydrofuran and 20 mL methanol) was added 347 mg of 10% palladium hydroxide on carbon catalyst followed by acetic acid (1 mL of a 30% solution in water). The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 25 hours the flask was charged with an additional 320 mg catalyst and 1 mL of 30% acetic acid and re-subjected to hydrogen. After a total reaction time of 3 days, the mixture was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (hexane:ethyl acetate, 1:1) gave the title compound (1.16 g).

Workup

  1. customevacuated
  2. additionAfter 25 hours the flask was charged with an additional 320 mg catalyst and 1 mL of 30% acetic acid
  3. customAfter a total reaction time of 3 days, the mixture was flushed with nitrogen
  4. filtrationfiltered over diatomaceous earth
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (hexane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-81b1587f0139408dbbc8f7a7ac40fa41
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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